9-Amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts
Wenwen Peng1, Jingwei Wan, Bing Xie
1College of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, P. R. China. zcj123@swu.edu.cn.
Abstract:
A new class of 9-amino-(9-deoxy)cinchona alkaloid-derived chiral phase-transfer catalysts bearing amino groups was developed by using known cinchona alkaloids as the starting materials. Due to the transformation of the 9-hydroxyl group into a 9-amino functional group, the catalytic performances were significantly improved in comparison with the corresponding first generation phase-transfer catalysts, and excellent yields (92-99%) and high enantioselectivities (87-96% ee) were achieved in the benchmark asymmetric α-alkylation of glycine Schiff base. Based on the special contribution of the amino group to the high yield and enantioselectivity, the possible catalytic mechanism was conjectured.
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